Synthesis of N-homobicyclic dideoxynucleoside analogues

Synthesis of N-homobicyclic dideoxynucleoside analogues

Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisom...

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Veröffentlicht in:Carbohydrate research 2012-05, Vol.352, p.191-196
Hauptverfasser: Raghavendra Swamy, N., Suryakiran, N., Paradesi Naidu, P., Venkateswarlu, Y.
Format: Artikel
Sprache:eng
Schlagworte:
Bridged Bicyclo Compounds - chemistry
Chemistry Techniques, Synthetic - methods
crystallization
d-Mannose
Dideoxynucleosides - chemical synthesis
Dideoxynucleosides - chemistry
iodides
mannose
N-Homobicyclic dideoxy nucleosides
nucleosides
Palladium(II) chloride
stereoisomers
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Zusammenfassung:Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2012.01.018